Maleic anhydride
- Formula: C4H2O3
- Molecular weight: 98.0569
- IUPAC Standard InChI: InChI=1S/C4H2O3/c5-3-1-2-4(6)7-3/h1-2H
- IUPAC Standard InChIKey: FPYJFEHAWHCUMM-UHFFFAOYSA-N
- CAS Registry Number: 108-31-6
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: 2,5-Furandione; cis-Butenedioic anhydride; Dihydro-2,5-dioxofuran; Maleic acid anhydride; Toxilic anhydride; Maleic anhydride, briquettes; Anhydrid kyseliny maleinove; Maleinanhydrid; Rcra waste number U147; UN 2215; 2,5-Furanedione; M 188; NSC 137651
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Glushko Thermocenter, Russian Academy of Sciences, Moscow
Constant pressure heat capacity of gas
| Cp,gas (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 83.94 | 273.15 | Caminati W., 1985 | Other statistically calculated values are: S(298.15 K)=300.75 J/mol*K and Cp(298.15 K)=88.87 J/mol*K [ Joshi R.M., 1970]. |
| 90.04 | 298.15 | ||
| 128.54 | 500. | ||
| 159.65 | 800. |
Condensed phase thermochemistry data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | -470.41 ± 0.71 | kJ/mol | Ccb | Wilhoit and Shiao, 1964 | ALS |
| ΔfH°solid | -469.6 ± 0.3 | kJ/mol | Ccb | Parks, Mosley, et al., 1950 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -1389.5 ± 0.67 | kJ/mol | Ccb | Wilhoit and Shiao, 1964 | Corresponding ΔfHºsolid = -470.41 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
| ΔcH°solid | -1390.3 ± 0.71 | kJ/mol | Ccb | Parks, Mosley, et al., 1950 | Corresponding ΔfHºsolid = -469.57 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of solid
| Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 119.9 | 300. | DeWit, DeKruif, et al., 1983 | T = 90 to 350 K. Linearly extrapolated.; DH |
| 123.2 | 310. | DeWit, Offringa, et al., 1983 | T = 300 to 450 K.; DH |
| 67.4 | 298.15 | Marchidan and Ciopec, 1978 | T = 298 to 480 K.; DH |
Reaction thermochemistry data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
+
=
By formula: C4H2O3 + C5H6 = C9H8O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -104. ± 2. | kJ/mol | Cm | Breslauer and Kabakoff, 1974 | liquid phase; solvent: Dioxane |
| ΔrH° | -107.9 | kJ/mol | Cm | Rogers and Quan, 1973 | liquid phase; Gas phase Diels-Alder |
+
=
By formula: C4H2O3 + C14H10 = C18H12O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -93. ± 2. | kJ/mol | Cm | Kiselev, Mavrin, et al., 1982 | liquid phase; solvent: Benzene |
| ΔrH° | -93.7 | kJ/mol | Eqk | Lenz, Hegedus, et al., 1982 | liquid phase; solvent: 1,2,4-C6H3Cl3 |
+
=
By formula: C4H2O3 + C5H6O = C9H8O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -58.5 | kJ/mol | Cm | Balbi, 1991 | liquid phase; solvent: Dioxane |
| ΔrH° | -60. | kJ/mol | Cm | Sparks and Poling, 1983 | solid phase; solvent: Dioxane |
+
=
By formula: C4H2O3 + H2O = C4H4O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -34.9 ± 0.8 | kJ/mol | Cm | Conn, Kistiakowsky, et al., 1942 | liquid phase; Heat of hydroysis at 303 K |
+
= C24H16O3
By formula: C4H2O3 + C20H14 = C24H16O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -427.2 | kJ/mol | Eqk | Lenz, Hegedus, et al., 1982 | liquid phase; solvent: 1,2,4-C6H3Cl3 |
=
+
By formula: C8H8O3 = C4H6 + C4H2O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 283.62 ± 0.96 | kJ/mol | Cm | Ghitau, Ciopec, et al., 1983 | solid phase; At 65 to 90°C |
+
=
By formula: C4H2O3 + C4H10O = C8H12O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -39. | kJ/mol | Kin | Merca, Poraicu, et al., 1978 | solid phase; solvent: n-Butanol; DTA |
+
=
By formula: C4H6 + C4H2O3 = C8H8O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -283.62 | kJ/mol | Cm | Ghitau, Ciopec, et al., 1983 | liquid phase |
+
=
By formula: C4H2O3 + C3H8O = propyl hydrogen maleate
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -35. | kJ/mol | Kin | Tribunescu, Poraicu, et al., 1978 | liquid phase |
+
=
By formula: C6H6BrN + C4H2O3 = C10H8BrNO3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 14. | kJ/mol | Cm | Srivastava, 1979 | solid phase |
+
=
By formula: C6H6ClN + C4H2O3 = C10H8ClNO3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 13. | kJ/mol | Cm | Srivastava, 1979 | solid phase |
=
+
By formula: C9H2Cl6O3 = C4H2O3 + C5Cl6
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 315. | kJ/mol | Ion | Vijayakumar and Fink, 1983 | solid phase |
Gas phase ion energetics data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
B - John E. Bartmess
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| 1.440 ± 0.087 | TDEq | Paul and Kebarle, 1989 | ΔGea(423 K) = -32.8±1 kcal/mol, ΔS = -1±3 eu.; B |
| 1.440 ± 0.048 | IMRE | Fukuda and McIver, 1985 | ΔGea(355 K) = -32.7 kcal/mol; ΔSea =-1.3, est. from data in Paul and Kebarle, 1989; B |
| 1.40 ± 0.20 | NBIE | Compton, Reinhardt, et al., 1974 | Lifetime: Cooper and Compton, 1973; B |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 11.07 | PE | Kimura, Katsumata, et al., 1981 | Vertical value; LLK |
| 11.11 ± 0.05 | PE | Galasso, Colonna, et al., 1977 | Vertical value; LLK |
| 11.1 | PE | Almemark, Backvall, et al., 1974 | Vertical value; LLK |
| 11.45 | PE | Bain and Frost, 1973 | Vertical value; LLK |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Caminati W., 1985
Caminati W.,
A study of the ring-bending and ring-twisting motions in maleic anhydride by rotational analysis of the corresponding vibrational satellites,
Spectrochim. Acta, 1985, A41, 937-941. [all data]
Joshi R.M., 1970
Joshi R.M.,
Thermodynamic properties of some monomeric compounds in the standard ideal gas state,
J. Polym. Sci., Part A-2, 1970, 8, 679-687. [all data]
Wilhoit and Shiao, 1964
Wilhoit, R.C.; Shiao, D.,
Thermochemistry of biologically important compounds. Heats of combustion of solid organic acids.,
J. Chem. Eng. Data, 1964, 9, 595-599. [all data]
Parks, Mosley, et al., 1950
Parks, G.S.; Mosley, J.R.; Peterson, P.V., Jr.,
Heats of combustion and formation of some organic compounds containing oxygen,
J. Chem. Phys., 1950, 18, 152. [all data]
DeWit, DeKruif, et al., 1983
DeWit, H.G.M.; DeKruif, C.G.; Van Miltenburg, J.C.,
Thermodynamic properties of molecular organic crystals containing organic crystals containing nitrogen, oxygen, and sulfur. II. Molar heat capacities of eight compounds by adiabatic calorimetry,
J. Chem. Thermodynam., 1983, 15, 891-902. [all data]
DeWit, Offringa, et al., 1983
DeWit, H.G.M.; Offringa, J.C.A.; De Kruif, C.G.; Van Miltenburg, J.C.,
Thermodynamic properties of molecular organic crystals containing nitrogen, oxygen and sulfur. III. Molar heat capacities measured by differential scanning calorimetry,
Thermochim. Acta, 1983, 65, 43-51. [all data]
Marchidan and Ciopec, 1978
Marchidan, D.I.; Ciopec, M.,
Thermodynamic properties of maleic, trimellitic and pyromellitic anhydrides,
Rev. Roum. Chim., 1978, 23, 19-29. [all data]
Breslauer and Kabakoff, 1974
Breslauer, K.J.; Kabakoff, D.S.,
Enthalpy of the Diels-Alder reaction of cyclopentadiene and maleic anhydride,
J. Org. Chem., 1974, 39, 721-722. [all data]
Rogers and Quan, 1973
Rogers, F.E.; Quan, S.W.,
Thermochemistry of the Diels-Alder reaction. III. Heat of addition of cyclopentadience to maleic anhydride,
J. Phys. Chem., 1973, 77, 828-831. [all data]
Kiselev, Mavrin, et al., 1982
Kiselev, V.D.; Mavrin, G.V.; Konovalov, A.I.,
Thermodynamic principles of the occurrence of a Diels-Alder reaction in the presence of a Lewis acid,
Zh. Org. Khim., 1982, 18, 2505-2510. [all data]
Lenz, Hegedus, et al., 1982
Lenz, T.G.; Hegedus, L.S.; Vaughan, J.D.,
Liquid phase thermochemical energy conversion systems - an application of Diels-Alder chemistry,
Int. J. Energy Res., 1982, 6, 357-365. [all data]
Balbi, 1991
Balbi, N.,
Dynamic calorimetry in the study of Diels-Alder reaction,
Calorim. Anal. Therm., 1991, 22, 299-304. [all data]
Sparks and Poling, 1983
Sparks, B.G.; Poling, B.E.,
Energy storage capacity of reversible liquid-phase Diels Alder reaction between maleic anhydride and 2-methyl furan,
Am. Inst. Chem. Eng. Symp. Ser. (AIChE Symp. Ser.), 1983, 29, 534-537. [all data]
Conn, Kistiakowsky, et al., 1942
Conn, J.B.; Kistiakowsky, G.B.; Roberts, R.M.; Smith, E.A.,
Heats of organic reactions. XIII. Heats of hydrolysis of some acid anhydrides,
J. Am. Chem. Soc., 1942, 64, 1747-17. [all data]
Ghitau, Ciopec, et al., 1983
Ghitau, M.; Ciopec, M.; Pintea, O.,
Study on Diels-Alder reaction for the synthesis of tetrahydrophthalic anhydride,
Rev. Chim. (Bucharest), 1983, 34, 299-305. [all data]
Merca, Poraicu, et al., 1978
Merca, E.; Poraicu, M.; Tribunescu, P.,
Kinetics of maleic monoester formation with n-butanol,
Bull. Stiint. Teh. Inst. Politeh. "Traian Vuia" Timisoara, Ser. Chim., 1978, 23, 160-163. [all data]
Tribunescu, Poraicu, et al., 1978
Tribunescu, P.; Poraicu, M.; Merca, E.; Facsko, O.,
Kinetics of mono-N-propylmaleate synthesis,
Bull. Stiint. Teh. Inst. Politeh. "Traian Vuia" Timisoara, Ser. Chim., 1978, 23, 147-151. [all data]
Srivastava, 1979
Srivastava, A.K.,
Solid-state reactions between maleic anhydride and substituted aromactic amines,
Z. Phys. Chem. (Leipzig), 1979, 260, 630-640. [all data]
Vijayakumar and Fink, 1983
Vijayakumar, C.T.; Fink, J.K.,
Heat of formation of the Diels-Alder adduct of hexachlorocyclopentadiene and maleic anhydride by appearance-energy measurements,
Org. Mass Spectrom., 1983, 18, 134. [all data]
Paul and Kebarle, 1989
Paul, G.; Kebarle, P.,
Electron Affinities of Cyclic Unsaturated Dicarbonyls: Maleic Anhydrides, Maleimides, and Cyclopentendione,
J. Am. Chem. Soc., 1989, 111, 2, 464, https://doi.org/10.1021/ja00184a009
. [all data]
Fukuda and McIver, 1985
Fukuda, E.K.; McIver, R.T., Jr.,
Relative electron affinities of substituted benzophenones, nitrobenzenes, and quinones. [Anchored to EA(SO2) from 74CEL/BEN],
J. Am. Chem. Soc., 1985, 107, 2291. [all data]
Compton, Reinhardt, et al., 1974
Compton, R.N.; Reinhardt, P.W.; Cooper, C.D.,
Mass spectrometry utilizing collisional ionization of cesium: Maleic anhydride and succinic anhydride,
J. Chem. Phys., 1974, 60, 2953. [all data]
Cooper and Compton, 1973
Cooper, C.D.; Compton, R.N.,
Electron attachment and cesium collisional ionization studies of tetrafluorosuccinic and hexafluoroglutaric anhydrides: Molecular electron affinities,
J. Chem. Phys., 1973, 59, 3550. [all data]
Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S.,
Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules
in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]
Galasso, Colonna, et al., 1977
Galasso, V.; Colonna, F.P.; Distefano, G.,
Photoelectron spectra of 1,2-indandione, 1,3-indandione and heterocyclic analogues,
J. Electron Spectrosc. Relat. Phenom., 1977, 10, 227. [all data]
Almemark, Backvall, et al., 1974
Almemark, M.; Backvall, J.E.; Moberg, C.A.; Akermark, B.; Asbrink, L.; Roos, B.,
Ab initio calculations and assignment of photoelectron spectra of maleic and succinic anhydride,
Tetrahedron, 1974, 30, 2503. [all data]
Bain and Frost, 1973
Bain, A.D.; Frost, D.C.,
Studies of the carbonyl group in some five-membered ring compounds by photoelectron spectroscopy,
Can. J. Chem., 1973, 51, 1245. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,gas Constant pressure heat capacity of gas Cp,solid Constant pressure heat capacity of solid EA Electron affinity ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
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